---
schema_version: "secwatch.filing_event.v1"
accession: "0001505155-23-000040"
form_type: "8-K"
ticker: "UPLD"
cik: "0001505155"
company_name: "Upland Software, Inc."
filed_at: "2023-05-03T23:59:59+00:00"
generated_at: "2026-06-16T00:58:07.522180+00:00"
event_type: "other_material"
sentiment: "neutral"
materiality_score: 0.6
calibrated_materiality_score: 0.6
confidence: "high"
source: SEC EDGAR
---

# Upland Software adopts poison pill to protect ~$147M in NOLs; triggers at 4.9% stake

## Summary
- As of March 31, 2023, Upland had approximately $147 million in U.S. federal net operating loss carryforwards (NOLs).
- Plan issues one right per share; rights become exercisable if a person/group acquires 4.9% or more of UPLD common stock without board approval.
- Rights expire May 1, 2024; board may redeem at $0.0001 per right prior to distribution date.
- Existing 4.9%+ holders may continue owning but cannot acquire additional shares without triggering the plan.
- Plan designed to deter an ownership change under Section 382 that would limit use of NOLs to offset future income tax.

## SEC filing metadata
- accession: 0001505155-23-000040
- form_type: 8-K
- ticker: UPLD
- cik: 0001505155
- company_name: Upland Software, Inc.
- filed_at: 2023-05-03T23:59:59+00:00
- event_type: other_material
- sentiment: neutral
- materiality_score: 0.6
- calibrated_materiality_score: 0.6
- confidence: high
- sec_items: 1.01, 3.03, 5.03, 7.01, 9.01
- EDGAR index: https://www.sec.gov/Archives/edgar/data/1505155/000150515523000040/0001505155-23-000040-index.htm
- EDGAR primary document: https://www.sec.gov/Archives/edgar/data/1505155/000150515523000040/upld-20230502.htm

## Machine-readable alternates
- HTML: https://secwatch.observer/filing/0001505155-23-000040
- JSON: https://secwatch.observer/filing/0001505155-23-000040.json
- Plain text: https://secwatch.observer/filing/0001505155-23-000040.txt

## Key facts
- Governance Changes
  Upland Software, Inc.: Certificate of Designations for Series B Junior Participating Preferred Stock filed with Delaware Secretary of State (effective 2023-05-02).
  - Change: charter amendment
  - Effective: 2023-05-02
  source text: In connection with the adoption of the Plan, the Board of Directors approved a Certificate of Designations of the Series B Junior Participating Preferred Stock (the “ Certificate of Designations ”). The Certificate of Designations was filed with the Secretary of State of the State of Delaware on May 2, 2023.
  evidence_url: https://www.sec.gov/Archives/edgar/data/1505155/000150515523000040/0001505155-23-000040-index.htm

This AI-assisted summary is a reading aid. Review the linked SEC EDGAR filing before relying on any specific claim.